Biocidal azolyl-propane nitriles

ABSTRACT

Azolyl-propanenitriles are disclosed, of the formula ##STR1## in which R is an aromatic hydrocarbon or an aromatic hydrocarbon substituted one or more times, the same or differently by halogen, (C 1  -C 4 )-alkyl, (C 1  -C 4 )-alkoxy, trifluoromethyl, cyano or nitro, R 1  is C 3  -C 8  cycloalkyl or C 3  -C 8  cycloalkyl substituted by C 1  -C 3  alkyl and 
     Y is N or CH, 
     and its acid addition salt with an inorganic or an organic acid, as well as processes for the production of these compounds and biocidal compositions containing the same. The compounds display fungicidal activity, growth-regulatory activity, and bactericidal activity.

BACKGROUND OF THE INVENTION

The invention concerns new azolyl-propane nitriles, processes for theproduction of these compounds, as well as biocidal compositionscontaining the same, and particularly those with fungicidal activity.

PATENT DISCLOSURE STATEMENT

Imidazolyl-propionitrile derivatives with fungicidal activity arealready known (DE-OS No. 26 04 047). However, these compounds display arelatively narrow activity spectrum which is unsatisfactory.

Imidazolyl-propionitriles with biocidal activity are likewise alreadyknown (DE-OS No. 31 25 780). Despite their fairly good effectiveness,there remains a need for compounds with still better characteristics.

OBJECT AND SUMMARY OF THE INVENTION

It is therefore an object according to the present invention to developnew propionitrile derivatives which open up broadly multiplied usepossibilities, particularly in the field of plant protection, and whichprovide greater fungicidal activity.

This object is obtained according to the present invention byazolyl-propane nitriles of the general formula ##STR2## in which R is anaromatic hydrocarbon or an aromatic hydrocarbon substituted at leastonce by the same or by different (C₁ -C₄)-alkyl, (C₁ -C₄)-alkoxy,trifluoromethyl, cyano or nitro R₁ is C₃ -C₈ -cycloalkyl or C₃ -C₈-cycloalkyl substituted by C₁ -C₃ -alkyl radicals and

Y is N or CH,

and their acid addition salts with inorganic or organic acid.

The compounds according to the present invention are in the broadestsense biocidally effective. They are characterized however, inparticular by a fungicidal activity which, in a surprising manner,exceeds that of known active substances of analogous constitution andactivity.

The fungicidal activity, surprisingly, is effective against fungi havingthe most different systematic structures. Used in treatment ofabove-ground plant parts, they protect against wind borne pathogens. Thecompounds also can be employed for the treatment of seed goods againstseed-transportable pathogens. Moreover, they work systematically, thatis, they are withdrawn by the roots of the plants, for example, afterapplication during the sowing, and are then transported into theabove-ground parts of the plants to protect the same against pathogens.

As further activities characteristic of the compounds according to thepresent invention, mention may be made of their growth-regulatory andbactericidal activities.

Because of their broad activity spectrum, the compounds according to thepresent invention are suitable not only for the protection of so-calledculture plants but also for the protection of materials and for thecontrol of human pathogenic and animal pathogenic microbes, andtherefore exhibit broadly multiplied use possibilities. Depending uponthe presence of specific substituents, the compounds according to thepresent invention display various outstanding activity. Thus, thecompounds can be employed as fungicides, and plant-growth regulators.The compounds according to the present invention also find use asplant-growth regulators which are characterized, for example, by thefollowing use possibilities:

Reduction in the vegetative growth of woody and weed plants, forexample, at road borders, railroad plants and the like, in order toprevent too abundant a growth. Reduction in growth grain in order toprevent depositing or breaking-off; and with cotton, in order toincrease the yield.

Influencing the branching of vegetative and generative organs withornamental or culture plants, in order to multiply the onset ofblooming; or with tobacco and tomato in order to reduce the developmentof side-shoots.

Improvement of the fruit quality, for example, increasing the sugarcontent of sugar beets, sugar cane or fruit; and a more uniform ripeningof the harvest goods, which leads to higher yields.

Increasing the resistance against climatic influences such as cold anddryness.

Influencing the latex flow of rubber plants.

Formation of parthenocarpic fruit, pollen sterility and sexual influenceare likewise possibilities of use.

Control of the germination of seeds or the driving out of buds.

Defoliation or influencing the fruit fall in order to facilitateharvesting.

The compounds according to the present invention are suitable inparticular for influencing the growth of beta beets. They also displaydesirable growth-regulatory effects with grain, soybeans and cotton.

The amounts of active compounds, depending upon specific use applied,range generally from 0.05 up to 5 kg of active substance per hectare.However, if necessary even higher application amounts can be employed.

The time of employment depends upon purpose of use and the climaticconditions.

In the compounds of general formula I, the substituents can represent,for example:

R is 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl,3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3-bromophenyl,4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl,2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl,3-ethylphenyl, 4-ethylphenyl, 2-propylphenyl, 3-propylphenyl,4-propylphenyl 2-isopropyphenyl, 3-isopropylphenyl, 4-isopropylphenyl,2-butylphenyl, 3-butylphenyl, 4-butylphenyl, 2-sec-butylphenyl,3-sec-butylphenyl, 4-sec-butylphenyl, 2-tert-butylphenyl,3-tert-butylphenyl, 4-tert-butylphenyl, 2-methoxyphenyl,3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl,4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl,4-methylthiophenyl, 2-ethylthiophenyl, 3-ethylthiophenyl,4-ethylthiophenyl 2-trifluromethylphenyl, 3-trifluormethylphenyl,4-trifluromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl,3-fluoro-4-methoxyphenyl, 3,4,5-trimethoxyphenyl,5-chloro-2-nitrophenyl, 3-chloro-5-nitro phenyl or4-chloro-2-fluorophenyl

R₁ can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, 2-methylcyclopentyl, 2-methylcyclohexyl,2,2-dimethylcyclopentyl, or 2,2-dimethylcyclohexyl and

Y is N or CH.

Not only inorganic acids but organic acids can be used to form the acidaddition salts. These include the following:

hydrochloric acid and hydrobromic acid, phosphoric acid, sulfuric acid,particularly nitric acid, mono- and bi-functional carboxylic acid andhydroxycarboxylic acids, such as, for example, acetic acid, maleic acid,succinic acid, furmaric acid, tartaric acid, citric acid, salicylicacid, sorbic acid, lactic acid, as well as sulfonic acids such as forexample, p-toluene sulfonic acid and 1,5-naphthalene disulfonic acid.

The acid addition salts can be formed by customary salt formationtechniques, for example, by dissolving a compound of formula I in asuitable solvent and then adding the acid.

An outstanding fungicidal activity is displayed for example, by thefollowing compounds:

2-(4-chlorophenyl)-2-cyclopentyloxy-3-(imidazol-1-yl)-propanenitrile andthe hydronitrate;2-(4-chlorophenyl)-2-cyclopentyloxy-3-(1,2,4-triazol-1-yl)-propanenitrileand the hydronitrate;2-cyclopentyloxy-3-(imidazol-1-yl)-2-(2-methylphenyl)-propanenitrile andthe hydronitrate;2-cyclopentyloxy-2-phenyl-3-(1,2,4-triazol-1-yl)-propanenitrile, and thehydronitrate;2-(2-chlorophenyl)-2-cyclopentyloxy-3-(1,2,4-triazol-1-yl)-propane-nitrileand the hydronitrate;2-cyclopentyloxy-3-(imidazol-1-yl)-2-phenyl-propanenitrile, and thehydronitrate.

Aside from the above-designated activities, the compounds according tothe present invention also are bactericidal which allows furtherpossibilities of employment.

The compounds according to the present invention can be used eitheralone or in mixture with one another or with other active substances. Ifnecessary, other plant-protection or pest-control agents can be added,according to the desired purpose.

The active substances of the invention or their mixtures are employed inthe form of preparation such as powders, spray agents, granulates,solutions, emulsions or suspensions, with the addition of liquid and/orsolid carrier material, respectively, diluting agents and, if necessary,wetting, adhering, emulsifying and/or dispersing adjuvants.

Suitable liquid carrier substances include, for example, water,aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene,cyclohexanone, isophorone, dimethylsulfoxide, dimethylformamide,moreover, mineral oil fractions and plant oils.

Suitable as solid carrier materials are mineral earths, for exampletonsil, silica gel, talcum, kaolin, attapulgite, limestone, silicic acidand plant products, for example, meal.

Examples of surface-active substances include: calcium lignin sulfonateand their salts, formaldehyde condensate, fatty alcohol sulfate, as wellas substituted benzene sulfonic acids and their salts.

Insofar as the active substances are supposed to be employed fordisinfection of seed goods, dyes can be admixed in order to provide thepickledseed goods with a clearly visible coloration.

The portion of the active substance in the various preparations canrange within broad limits. For example, the composition can contain fromabout 10 to 90 percent by weight active substance, about 90 to 10percent weight liquid or solid carrier material, as well as, ifnecessary, up to 20 percent by weight of surface-active substance, uponcorresponding reduction in the amount of carrier.

The present composition can be applied in known manner, for example,with water as the carrier in spray amounts of about 100 up to about10,000 liter/ha. The compositions also can be used in the so-calledlow-volume or ultra-low-volume techniques, and in the form ofmicrogranulates.

By way of non-limiting examples, the following typify the compounds ofthe invention.

A. Spray Powder

(a)

40 percent by weight active substance

25 percent by weight clay mineral

20 percent by weight silicic acid

10 percent by weight cell pitch

5 percent by weight surface-active substance based upon a mixture of thecalcium salt of lignin sulfonic acid, alkylphenolpolyglycolether

(b)

20 percent by weight active substance

60 percent by weight kaolin

15 percent by weight silicic acid

5 percent by weight surface-active substance based upon the sodium saltof N-methyl-N-oleyltaurine and the calcium salt of lignin sulfonic acid

(c)

10 percent by weight active substance

60 percent by weight clay minerals

15 percent by weight silicic acid

10 percent by weight cell pitch

5 percent by weight surface-active substance based upon the sodium saltof N-methyl-N-oleyltaurine and the calcium salt of lignin sulfonic acid

B. Paste

45 percent by weight active substance

5 percent by weight sodium aluminum silicate

15 percent by weight cetylpolyglycolether with 8 mol ethylenoxide

2 percent by weight spindle oil

10 percent by weight polyethyleneglycol

23 parts water

C. Emulsion Concentrate

25 percent by weight active substance

15 percent by weight cyclohexanol

55 percent by weight xylene

5 percent by weight mixture of nonylphenylpolyoxyethylene or calciumdodecylbenzene sulfonate

The new compounds according to the present invention can be produced byreacting compounds of the general formula ##STR3## with compounds of thegeneral formula ##STR4## or their alkali salts in the presence of asolvent and, if necessary, in the presence of a base, whereby R, R₁ andY have the above given meaning, and X is halogen, alkylsulfonyloxy orarylsulfonyloxy, or alkylsulfonyloxy or arylsulfonyloxy halogenated in aside chain.

Examples of halogen include chlorine, bromine or iodine; methyl, ethyl,propyl and trifluoromethylsulfonyl are suitable as alkylsulfonyloxy;whereas examples of arylsulfonyloxy include benzene sulfonyloxy andp-toluene sulfonyloxy.

When a solvent is employed it is desirable to select a material which isinert with respect to the reactants, preferably polar, aproticsubstances such as N,N-dimethylformamide, N-methylpyrrolidone,tetramethylurea, hexamethylphosphoric acid triamide anddimethylsulfoxide, and even higher boiling aromatic and aliphatichydrocarbons such as toluene, fluorobenzene, or xylene. The reactiontemperature can be varied within broad limits. Preferably a temperaturebetween 100° C. and 200° C. is used. The reactions follow under normalor excess pressure.

The novel features which are considered as characteristics of theinvention are set forth in particular in the appended claims. Theinvention itself, however, both as to its construction and its method ofoperation, together with additional objects and advantages thereof, willbe best understood from the following description of specificembodiments.

DESCRIPTION OF PREFERRED EMBODIMENTS Example 12-cyclopentyloxy-3-(imidazol-1-yl)-2-(methylphenyl)-propanenitrile,hydronitrate

60.7 g (0.188 mol)2-cyclopentyloxy-2-(2-methylphenyl)-3-methylsulfonyloxy-propanenitrile,63.9 g (0.938 mol) imidazole and 3.88 ml DMF are stirred for six hoursat 160° C. bath temperature. They are then poured into 200 ml water,extracted twice--each time with 200 ml methylene chloride--and theorganic phase is then dried with MgSO₄. It is then rotated in a vacuumafter which the oil is dissolved in 100 ml isopropanol and then reacteddropwise with 10 ml 100% nitric acid, with cooling with ice. Nextfollows 20 minutes after-stirring with RT, addition of 200 ml aceticester, and evacuation in a vacuum. In this manner 30.7 g of the titlecompound are obtained, MP: 160° C. (decomposition).

Example 22-cyclopentyloxy-3-(imidazol-1-yl)-2-(methylphenyl)-propanenitrile

28.5 g of the hydronitrate obtained in Example 1 are dissolved in 300 mlmethanol. Within a period of 5 minutes and at a temperature of between5° and 15° C., 100 ml dilute ammonia solution are added dropwise. Themixture is then diluted with 750 ml water and extracted twice, each timewith 300 ml ethyl acetate. Then follows drying with MgSO₄, centrifugingto dryness, and reaction of the remaining oil with 200 ml hexane,whereafter crystallization occurs. In this manner are obtained 21.7 g ofthe title compound, MP: 92° C.

Example 32-cyclohexyloxy-2-(2-methylphenyl)-3-(1,2,4-triazol-1-yl)-propanenitrile,hydronitrate

9.8 g of 1,2,4-triazol are heated in a mixture of 120 mldimethylsulfoxide and 70 ml xylene with 5.7 g NaOH-tablets for two hoursat 180° C. bath temperature. Reaction water is removed in a waterseparator. The bath temperature is then allowed to drop to 150° C., and32 g of2-cyclohexyloxy-3-methansulfonyl-2-(2-methylphenyl)-propanenitrile and alittle DMSO are added to the reaction mixture. After stirring for threehours at 150° C., ice-water is aded, followed by two extractions, eachtime with 200 ml methylene chloride, whereupon the organic phase iswashed again with 100 ml H₂ O. Then follows drying with MgSO₄, spinning,take up in 70 ml isopropanol and dropwise reaction under ice coolingwith 3.9 ml. 100% nitric acid. The reaction mixture is then reacted with50 ml ether, evacuated in a vacuum and then recrystallized fromisopropanol. 14.36 g of the title compound are obtained, with meltingpoint 194° -197° C. (decomposition).

In analogous manner, using appropriate starting materials the followingcompounds according to the present invention are prepared:

    ______________________________________                                        Ex-                                                                           am-                                                                           ple  Name of Compound     Physical Constant                                   ______________________________________                                         4   2-cyclopentyloxy-2-(2-methyl-                                                                      MP: 142-144° C. (D)                               phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile, hydeonitrate                                              5   2-cyclohexyloxy-3-(imidazol-1-                                                                     MP: 150-152° C. (D)                               yl)-2-(2-methylphenyl)-propane-                                               nitrile, hydronitrate                                                     6   2-cyclohexyloxy-3-(imidazol-1-                                                                     MP: 114-116° C.                                   yl)-2-(2-methylphenyl)-propane-                                               nitrile                                                                   7   2-cyclohexyloxy-2-(2-methyl-                                                                       MP: 82-85° C.                                     phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile                                                            8   2-cyclohexyloxy-3-(imidazol-1-                                                                     MP: 75° C.                                        yl)-2-phenyl-propanenitrile                                               9   2-cyclohexyloxy-3-(imidazol-1-                                                                     MP: 211-212° C. (D)                               yl)-2-phenyl-propanenitrile,                                                  hydronitrate                                                             10   2-(2-chlorophenyl)-2-cyclohexyl-                                                                   MP: 128° C.                                       oxy-3-(imidazol-1-yl)-propane-                                                nitrile                                                                  11   2-(2-chlorophenyl)-2-cyclohexyl-                                                                   MP: 186-188° C. (D)                               oxy-3-(imidazol-1-yl)-propane-                                                nitrile, hydronitrate                                                    12   2-cyclohexyloxy-2-phenyl-3-                                                                        MP: 94-97° C.                                     (1,2,4-triazol-1-yl)-propane-                                                 nitrile                                                                  13   2-cyclohexyloxy-2-phenyl-3-                                                                        MP: 185-186° C. (D)                               (1,2,4-triazol-1-yl)-propane-                                                 nitrile, hydronitrate                                                    14   2-(4-chlorophenyl)-2-cyclohexyl-                                                                   MP: 214-215° C. (D)                               oxy-3-(imidazol-1-yl)-propane-                                                nitrile, hydronitrate                                                    15   2-(2-chlorophenyl)-2-cyclohexyl-                                                                   MP: 109-112° C.                                   oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile                                                                  16   2-(2-chlorophenyl)-2-cyclohexyl-                                                                   MP: 139°  C. (D)                                  oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile, hydronitrate                                                    17   2-cyclopentyloxy-3-(imidazol-1-                                                                    n.sub.D.sup.20 : 1.5462                                  yl)-2-phenyl-propanenitrile                                              18   2-cyclopentyloxy-3-(imidazol-1-                                                                    MP: 164-167° C. (D)                               yl)-2-phenyl-propanenitrile,                                                  hydronitrate                                                             19   2-(2-chlorophenyl)-2-cyclopentyl-                                                                  n.sub.D.sup.20 : 1.5590                                  oxy-3-(imidazol-1-yl)-propane-                                                nitrile                                                                  20   2-(2-chlorophenyl)-2-cyclopentyl-                                                                  MP: 130° C. (D)                                   oxy-3-imidazol-1-yl)-propane-                                                 nitrile, hydronitrate                                                    21   2-cyclopentyloxy-2-phenyl-3-                                                                       MP: 85-88° C.                                     (1,2,4-triazol-1-yl)-propane-                                                 nitrile                                                                  22   2-cyclopentyloxy-2-phenyl-3-                                                                       MP: 172-174° C.                                   (1,2,4-triazol-1-yl)-propane-                                                 nitrile, hydronitrate                                                    23   2-(2-chlorophenyl)-2-cyclopentyl-                                                                  MP: 91-94° C.                                     oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile                                                                  24   2-(2-chlorophenyl)-2-cyclopentyl-                                                                  MP: 136° C. (D)                                   oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile, hydronitrate                                                    25   2-cyclohexyloxy-2-(2,4-dichloro-                                                                   n.sub.D.sup.20 : 1.5565                                  phenyl)-3-(imidazol-1-yl)-                                                    propanenitrile                                                           26   2-cyclohexyloxy-2-(2,4-dichloro-                                                                   MP: 156° C. (D)                                   phenyl)-3-(imidazol-1-yl)-                                                    propanenitrile, hydronitrate                                             27   2-(4-chlorophenyl)-2-cyclohexyl-                                                                   MP: 97° C. (D)                                    oxy-3-(1,2,4-triazol-1-yl)-                                                   propanenitrile                                                           28   2-(4-chlorophenyl)-2-cyclohexyl-                                                                   MP: 176-178° C. (D)                               oxy-3-(1,2,4-triazol-1-yl)-                                                   propanenitrile, hydronitrate                                             29   2-cyclohexyloxy-2-(2,4-dichloro-                                                                   MP: 121-124° C.                                   phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile                                                           30   2-cyclohexyloxy-2-(2,4-dichloro-                                                                   MP: 145-148° C. (D)                               phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile, hydronitrate                                             31   2-(4-chlorophenyl)-2-cyclopentyl-                                                                  MP: 100-102° C.                                   oxy-3-(imidazol-1-yl)-propane-                                                nitrile                                                                  32   2-(4-chlorophenyl)-2-cyclopentyl-                                                                  MP: 200-201° C. (D)                               oxy-3-(imidazol-1-yl)propane-                                                 nitrile, hydronitrate                                                    33   2-(4-chlorophenyl)-2-cyclopentyl-                                                                  MP: 89-92° C.                                     oxy-3-(1,2,4-triazol-1-yl)-                                                   propanenitrile                                                           34   2-(4-chlorophenyl)-2-cyclopentyl-                                                                  MP: 162-165° C. (D)                               oxy-3-(1,2,4-triazol-1-yl)-                                                   propanenitrile, hydronitrate                                             35   2-cyclopentyloxy-2-(2-fluorophenyl)-                                                               n.sub.D.sup.20 : 1.5328                                  3-(imidazol-1-yl)-propanenitrile                                         36   2-cyclopentyloxy-2-(2-fluorophenyl)-                                                               MP: 60-62° C.                                     3-(1,2,4-triazol-1-yl)-propanenitrile                                    37   2-cyclohexyloxy-2-(2-fluorophenyl)-                                                                n.sub.D.sup.20 :1.5300                                   3-(imidazol-1-yl)-propanenitrile                                         38   2-cyclohexyloxy-2-(2-fluorophenyl)-                                                                MP: 80-82° C.                                     3-(1,2,4-triazol-1-yl)-propanenitrile                                    39   2-cyclopentyloxy-2-(2-fluorophenyl)-                                                               MP: 165-168° C. (D)                               3-(imidazol-1-yl)-propanenitrile,                                             hydronitrate                                                             40   2-cyclohexyloxy-2-(2-fluorophenyl)-                                                                MP: 205-206° C. (D)                               3-(imidazol-1-yl)-propanenitrile,                                             hydronitrate                                                             41   2-cyclopentyloxy-2-(2-methylphenyl)-                                                               MP: 78-81° C.                                     3-(1,2,4-triazol-1-yl)-propanenitrile                                    ______________________________________                                         (D) = Decomposition                                                      

The azolyl propanenitriles according to the present invention, as wellas their acid addition salts, are nearly colorless and odorless oils orsolids. The salts are slightly soluble in water but soluble in polarorganic solvents such as acetonitrile, N,N-dimethylformamide, loweralcohols, chloroform and methylene chloride. The free bases dissolvepoorly in water and more or less well in organic solvents such as, forexample, alcohols, ethers or chlorinated hydrocarbons.

The starting materials, are 3-aryl-respectively3-alkylsulfonyloxy-propanenitriles of the general formula II, with Xrepresenting aryl-respectively alkylsulfonyloxy have not previously beendescribed in the literature. They are obtained by hydroxymethylating inknown manner, already known phenyl acetonitriles of the general formula##STR5## wherein R and R₁ have the above-given meanings, to obtain3-hydroxypropanenitrile of the general formula ##STR6## which arereacted with suitable sulfonic acid derivatives, such as, for example,sulfonic acid chloride, if necessary with the addition of an acidbinder. The hydroxy methyl compounds of general formula IV were notpreviously disclosed in the literature. The phenyl-acetonitrile of thegeneral formula III are obtained by reaction of O-sulfonatedcyanohydrine with the corresponding alcohol R₁ OH.

The following examples serve to illustrate various utilities for thecompounds according to the present invention.

The actual concentration of the active substances used is given in ppm(parts per million of spray liquid). The fungicidal activity iscalculated in the following Examples from infection data determined ineach instance, as follows: ##EQU1##

Example 42

Effect of Prophylactic Leaf Treatment Against Real Mildew Erysiphegraminis on Barley in a Greenhouse.

Young barley plants in the stage of the first leaves are sprayeddripping wet with the given concentrations. After drying of the spraycoating, the treated plants as well as untreated control plants areinnoculated with dry mildew spores by stroking the test plants withinfected plants. Thereafter the test plants are cultivated in agreenhouse at about 20°-22° C., and one week later the percentage ofinfection on the leaf surfaces is determined. The excellent activitiesof the compounds according to the present invention are evident from thefollowing test data:

    ______________________________________                                                         % Activity                                                                    Against Erysiphe                                                              graminis with Active                                                          Substance Concentration                                      Compound           250     25     2.5   ppm                                   ______________________________________                                        2-cyclopentyloxy-3-(imidazol-1-                                                                  100     100    100                                         yl)-2-(2-methylphenyl)-propane-                                               nitrile, hydronitrate                                                         2-cyclopentyloxy-2-(2-methyl-                                                                    100     100     98                                         phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile, hydronitrate                                                  2-cyclohexyloxy-3-(imidazol-1-                                                                   100     100    100                                         yl)-2-(2-methylphenyl)-propane-                                               nitrile, hydronitrate                                                         2-cyclohexyloxy-2-(2-methyl-                                                                     100     100    >90                                         phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile, hydronitrate                                                  2-cyclohexyloxy-3-(imidazol-1-                                                                   100     100    100                                         yl)-2-(2-methylphenyl)-propane-                                               nitrile                                                                       2-cyclohexyloxy-2-(2-methyl-                                                                     100     100    >90                                         phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile                                                                2-cyclopetyloxy-3-(imidazol-1-                                                                   100     100    100                                         yl)-2-(2-methylphenyl)-propane-                                               nitrile                                                                       2-cyclopentyloxy-2-(2-methylphenyl)-                                                             100     100    100                                         3-(1,2,4-triazol-1-yl)-propanenirile                                          2-cyclohexyloxy-3-(imidazol-1-                                                                   100     100    100                                         yl)-2-phenyl-propanenitrile                                                   2-cyclohexyloxy-3-(imidazol-1-                                                                   100     100    100                                         yl)-2-phenyl-propanenitrile, hydro-                                           nitrate                                                                       2-(2-chlorophenyl)-2-cyclohexyl-                                                                 100     100     95                                         oxy-3-(imidazol-1-yl)-propanenitrile                                          2-(2-chlorophenyl)-2-cyclohexyl-                                                                 100     100    100                                         oxy-3-(imidazol-1-yl)-propane-                                                nitrile, hydronitrate                                                         2-cyclohexyloxy-2-phenyl-3-                                                                      100     100     87                                         (1,2,4-triazol-1-yl)-propanenitrile                                           2-cyclohexyloxy-2-phenyl-3-                                                                      100     100    100                                         (1,2,4-triazol-1-yl)-propanenitrile,                                          hydronitrate                                                                  2-(4-chlorophenyl)-2-cyclohexyl-                                                                 100     100    100                                         oxy-3-(imidazol-1-yl)-propane-                                                nitrile, hydronitrate                                                         2-(2-chlorophenyl)-2-cyclohexyl-                                                                 100     100    100                                         oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile                                                                       2-(2-chlorophenyl)-2-cyclohexyl-                                                                 100     100    100                                         oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile, hydronitrate                                                         2-cyclopentyloxy-3-(imidazol-1-yl)-                                                              100     100     95                                         2-phenyl-propannitrile                                                        2-cyclopentyloxy-3-(imidazol-1-yl)-                                                              100     100    100                                         2-phenyl-propanenitrile, hydro-                                               nitrate                                                                       2-(2-chlorophenyl)-2-cyclopentyl-                                                                100     100    100                                         oxy-3-(imidazol-1-yl)-propanenitrile                                          2-(2-chlorophenyl)-2-cyclopentyl-                                                                100     100    100                                         oxy-3-(imidazol-1-yl)-propane-                                                nitrile, hydronitrate                                                         2-cyclopentyloxy-2-phenyl-3-                                                                     100     100    100                                         (1,2,4-triazol-1-yl)-propanenitrile                                           2-cyclopentyloxy-2-phenyl-3-                                                                     100     100    100                                         (1,2,4-triazol-1-yl)-propane-                                                 nitrile, hydronitrate                                                         2-(2-chlorophenyl)-2-cyclopentyl-                                                                100     100     87                                         oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile                                                                       2-(2-chlorophenyl)-2-cyclopentyl-                                                                100     100                                                oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile, hydronitrate                                                         2-cyclohexyloxy-2-(2,4-dichloro-                                                                 100     100     87                                         phenyl)-3-(imidazol-1-yl)-                                                    propanenitrile                                                                2-cyclohexyloxy-2-(2,4-dichloro-                                                                 100     100     88                                         phenyl)-3-(imidazol-1-yl)-                                                    propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclohexyl-                                                                 100     100    100                                         oxy-3-(1,2,4-triazol-1-yl)-                                                   propanenitrile                                                                2-(4-chlorophenyl)-2-cyclohexyl-                                                                 100     100     94                                         oxy-3-(1,2,4-triazol-1-yl)-                                                   propanenitrile, hydronitrate                                                  2-cyclohexyloxy-2-(2,4-dichloro-                                                                 100     100    100                                         phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile                                                                2-cyclohexyloxy-2-(2,4-dichloro-                                                                  98      94     92                                         phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclopentyl-                                                                100     100    100                                         oxy-3-(imidazol-1-yl)-propanenitrile                                          2-(4-chlorophenyl)-2-cyclopentyl-                                                                100     100    100                                         oxy-3-(imidazol-1-yl)-propane-                                                nitrile, hydronitrate                                                         2-(4-chlorophenyl)-2-cyclopentyl-                                                                100     100    100                                         oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile                                                                       2-(4-chlorophenyl)-2-cyclopentyl-                                                                100     100    100                                         oxy-3-(1,2,4-triazol-1-yl)-                                                   propanenitrile, hydronitrate                                                  ______________________________________                                    

The composition according to the invention is provided as a 10% or 20%formulation dispersible in water.

Example 43

Effect of Prophylactic Leaf Treatment Against Erysiphe Cichoracearumwith Pumpkin Plants in a Greenhouse.

Pumpkin plants sprayed dripping wet with the given active substanceconcentrations are innoculated by means of dusting with dry mildewspores of Erysiphe cichoracearum, after drying of the spray coatings,and then incubated in a greenhouse at 24° C., together with innoculatedbut untreated control plants. After one week, the infected leaf surfaceis estimated in percentage of the total leafe surface.

The designation "S" in the table signifies that the fungicidal activityis also accompanied by a growth of the plants (after the treatment) andis positively determined. That is, the active substances are transportedsystematically into the growth area of the plants, and there to, provide100% activity against mildew.

    ______________________________________                                                             % Activity Against                                                            Erysiphe cichoracearum                                   Compounds            with active substance                                    According to         concentration                                            the Invention        5       0.5     ppm                                      ______________________________________                                        2-cyclopentyloxy-3-(imidazol-                                                                      .sup. 100s                                                                            100                                              1-yl)-2-(2-methylphenyl)-pro-                                                 panenitrile, hydronitrate                                                     2-cyclopentyloxy-2-(2-methyl-                                                                      .sup. 100s                                                                            .sup. 100s                                       phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile, hydronitrate                                                  2-cyclohexyloxy-3-(imidazol-1-                                                                     .sup. 100s                                                                            100                                              yl)-2-(2-methylphenyl)-propane-                                               nitrile, hydronitrate                                                         2-cyclohexyloxy-2-(2-methyl-                                                                       .sup. 100s                                                                            .sup. 100s                                       phenyl)-3-(1,2,4-trizol-1-yl)-                                                propanenitrile, hydronitrate                                                  2-cyclohexyloxy-3-(imidazol-1-                                                                     .sup. 100s                                                                            100                                              yl)-2-(2-methylphenyl)-propane-                                               nitrile                                                                       2-cyclohexyloxy-2-(2-methyl-                                                                       .sup. 100s                                                                            .sup. 100s                                       phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile                                                                2-cyclopentyleoxy-3-(imidazol-1-                                                                   .sup. 100s                                                                            .sup. 100s                                       yl)-2-(2-methylphenyl)-propane-                                               nitrile                                                                       2-cyclopentyloxy-2-(2-methylphenyl)-                                                               .sup. 100s                                                                            .sup. 100s                                       3-(1,2,4-triazol-1-yl)-propane-                                               nitrile                                                                       2-cyclohexyloxy-3-(imidazol-1-                                                                     .sup. 100s                                                                            .sup. 100s                                       yl)-2-phenyl-propanenitrile                                                   2-cyclohexyloxy-3-(imidazol-1-                                                                     .sup. 100s                                                                            100                                              yl)-2-phenyl-propanenitrile,                                                  hydronitrate                                                                  2-(2-chlorophenyl)-2-cyclo-                                                                        100     100                                              hexyloxy-3-(imidazol-1-yl)-                                                   propanenitrile                                                                2-(2-chlorophenyl)-2-cyclo-                                                                        100     100                                              hexyloxy-3-(imidazol-1-yl)-                                                   propanenitrile, hydronitrate                                                  2-cyclohexyloxy-2-phenyl-3-                                                                        100     100                                              (1,2,4-triazol-1-yl)-propane-                                                 nitrile                                                                       2-(2-chlorophenyl)-2-cyclo-                                                                        100     100                                              hexyloxy-3-(1,2,4-triazol-1-                                                  yl)-propanenitrile                                                            2-(2-chlorophenyl)-2-cyclo-                                                                        100     100                                              hexyloxy-3-(1,2,4-triazol-1-                                                  yl)-propanenitrile, hydronitrate                                              2-cyclopentyloxy-3-(imidazol-1-                                                                    100     100                                              yl)-2-phenyl-propanenitrile                                                   2-cyclopentyloxy-3-(imidazol-1-                                                                    100     100                                              yl)-2-phenyl-propanenitrile,                                                  hydronitrate                                                                  2-(2-chlorphenyl)-2-cyclo-                                                                         100     100                                              pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile                                                                2-(2-chlorophenyl)-2-cyclo-                                                                        100      97                                              pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile, hydronitrate                                                  2-cyclopentyloxy-2-phenyl-3-                                                                       100     100                                              (1,2,4-triazol-1-yl)-propane-                                                 nitrile                                                                       2-cyclopentyloxy-2-phenyl-3-                                                                       100     100                                              (1,2,4-triazol-1-yl)-propane-                                                 nitrile, hydronitrate                                                         2-(2-chlorophenyl)-2-cyclo-                                                                         97      95                                              pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile                                                            2-(2-chlorophenyl)-2-cyclo-                                                                        100     100                                              pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile, hydronitrate                                              2-cyclohexyloxy-2-(2,4-dichloro-                                                                   100     100                                              phenyl)-3-(imidazol-1-yl)-propane-                                            nitrile                                                                       2-cyclohexyloxy-2-(2,4-dichloro-                                                                   100      98                                              phenyl)-3-(imidazol-1-yl)-propane-                                            nitrile, hydronitrate                                                         2-(4-chlorophenyl)-2-cyclohexyl-                                                                   100     100                                              oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile                                                                       2-(4-chlorophenyl)-2-cyclohexyloxy-                                                                100     100                                              3-(1,2,4-triazol-1-yl)-propane-                                               nitrile, hydronitrate                                                         2-cyclohexyloxy-2-(2,4-dichloro-                                                                   100     100                                              phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile                                                                2-cyclohexyloxy-2-(2,4-dichloro-                                                                   100      96                                              phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclopentyl-                                                                  100     100                                              oxy-3-(imidazol-1-yl)-propane-                                                nitrile                                                                       2-(4-chlorophenyl)-2-cyclopentyl-                                                                  100     100                                              oxy-3-(imidazol-1-yl)-propane-                                                nitrile, hydronitrate                                                         2-(4-chlorophenyl)-2-cyclopentyl-                                                                  .sup. 100s                                                                            100                                              oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile                                                                       2-(4-chlorophenyl)-2-cyclopentyl-                                                                  .sup. 100s                                                                            100                                              oxy-3-(1,2,4-triazol-1-yl)-propane-                                           nitrile, hydronitrate                                                         2-cyclohexyloxy-2-phenyl-3-(1,2,4-                                                                 100     100                                              triazol-1-yl)-propanenitrile hydro-                                           nitrate                                                                       2-(4-chlorophenyl)-2-cyclohexyl-                                                                   100     100                                              oxy-3-(imidazol-1-yl)-propane-                                                nitrile, hydronitrate                                                         Comparison agent      20      4      ppm                                      2-(1-methyl-n-heptyl)-4,6-                                                                           99.5    98.5                                           dinitrophenol-crotonate                                                       ______________________________________                                    

The compositions are provided as 20% formulations dispersible in water.

Example 44

Effect of Prophylactic Treatment Against Dwarf Rust Puccinia Hordei withBarley in a Climatized Plant-Growth Chamber.

Young barley plants in the stage of the first leaves are sprayed wetwith the given concentrations. After drying of the spray coatings, thetreated plants as well as untreated control plants are innoculated bymeans of stroking over with dwarf rust-infected plants. The test plantsare then placed in a plant-growth chamber. The plants are therecultivated for a period of ten days at 15° C., during the first two daysof which a nearly moisture-saturated air atmosphere is provided. Thenthe percent-portion of rust-infected leaf surface is estimated.

    ______________________________________                                                          % Activity Against Puccinia                                 Compounds         hordei with active Substance                                According         Concentration                                               to the Invention  500     250    25     ppm                                   ______________________________________                                        2-cyclopentyloxy-3-(imidazol-                                                                   100     100    >90                                          1-yl)-2-(2-methylphenyl)-pro-                                                 panenitrile, hydronitrate                                                     2-cyclopentyloxy-2-(2-methyl-                                                                   100      98    --                                           phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile, hydronitrate                                              2-cyclohexyloxy-3-(imidazol-1-                                                                  100     >90    --                                           yl)-2-(2-methyphenyl)-propane-                                                nitrile, hydronitrate                                                         2-cyclohexyloxy-2-(2-methyl-                                                                    100     --     --                                           phenyl)-2-(1,2,4-triazol-1-yl)-                                               propanenitrile, hydronitrate                                                  2-cyclohexyloxy-3-(imidazol-1-                                                                  100     --     --                                           yl)-2-(2-methylphenyl)-pro-                                                   panenitrile                                                                   2-cyclohexylox-2-(2-methyl-                                                                     100     --     --                                           phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile                                                            2-cyclopentyloxy-3-(imidazol-1-                                                                 100     100    --                                           yl)-2-(2-methylphenyl)-propane-                                               nitrile                                                                       2-cyclopentyloxy-2-(2-methyl-                                                                   100     100    --                                           phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile                                                            2-cyclohexyloxy-3-(imidazol-1-                                                                  100     100    --                                           yl)-2-phenyl-propanenitrile                                                   2-cyclohexyloxy-3-(imidazol-1-                                                                  --       95    --                                           yl)-2-phenyl-propanenitrile,                                                  hydronitrate                                                                  2-(2-chlorophenyl)-2-cyclo-                                                                     100     100    --                                           hexyloxy-3-(imidazol-1-yl)-                                                   propanenitrile                                                                2-(2-chlorophenyl)-2-cyclo-                                                                     --       98    --                                           hexyloxy-3-(imidazol-1-yl)-                                                   propanenitrile, hydronitrate                                                  2-cyclohexyloxy-2-phenyl-3-                                                                     --       98    --                                           (1,2,4-triazol-1-yl)-propane-                                                 nitrile                                                                       2-cyclohexyloxy-2-phenyl-3-                                                                     100     100    --                                           (1,2,4-triazol-1-yl)-propane-                                                 nitrile, hydronitrate                                                         2-(4-chlorophenyl)-2-cyclo-                                                                     100     100    90                                           hexyloxy-3-(imidazol-1-yl)-pro-                                               panenitrile, hydronitrate                                                     2-(2-chlorophenyl)-2-cyclo-                                                                     --       95    --                                           hexyloxy-3-(1,2,4-triazol-1-                                                  yl)-propanenitrile, hydronitrate                                              2-cyclopentyloxy-3-(imidazol-                                                                   100     100    90                                           1-yl)-2-phenyl-propanenitrile                                                 2-cyclopentyloxy-3-(imidazol-                                                                   100     100    --                                           1-yl)-2-phenyl-propanenitrile,                                                hydronitrate                                                                  2-(2-chlorophenyl)-2-cyclo-                                                                     --       95    93                                           pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile                                                                2-(2-chlorophenyl)-2-cyclo-                                                                     100     100    85                                           pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile, hydronitrate                                                  2-cyclopentyloxy-2-phenyl-                                                                      100     100    95                                           3-(1,2,4-triazol-1-yl)-                                                       propanenitrile                                                                2-cyclopentyloxy-2-phenyl-                                                                      --       95    --                                           3-(1,2,4-triazol-1-yl)-pro-                                                   panenitrile, hydronitrate                                                     2-(2-chlorophenyl)-2-cyclo-                                                                     100     100    85                                           pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile                                                          2-cyclohexyloxy-2-(2,4-                                                                         100     100    85                                           dichlorophenyl)-3-(imidazol-                                                  1-yl)-propanenitrile                                                          2-cyclohexyloxy-2-(2,4-                                                                         100     100    --                                           dichlorophenyl)-3-(imidazol-                                                  1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       2-(4-chlorophenyl)-2-cyclo-                                                                     100     100    --                                           hexyloxy-3-(1,2,4-triazol-1-                                                  yl)-propanenitrile                                                            2-(4-chlorophenyl)-2-cyclo-                                                                     100     100    95                                           hexyloxy-3-(1,2,4-triazol-1-                                                  yl)-propanenitrile, hydro                                                     nitrate                                                                       2-cyclohexyloxy-2-(2,4-                                                                         100     100    --                                           dichlorophenyl)-3-(1,2,4-                                                     triazol-1-yl)-propanenitrile                                                  2-cyclohexyloxy-2-(2,4-                                                                         --       95    --                                           dichlorophenyl)-3-(1,2,4-                                                     triazol-1-yl)-propane-                                                        nitrile, hydronitrate                                                         2-(4-chlorophenyl)-2-cyclo-                                                                     100     100    100                                          pentyloxy-3-(imidazol-1-                                                      yl)-propanenitrile                                                            2-(4-chlorophenyl)-2-cyclo-                                                                     100     100    100                                          pentyloxy-3-(imidazol-1-                                                      yl)-propanenitrile, hydronitrate                                              2-(4-chlorophenyl)-2-cyclo-                                                                     100     100    100                                          pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile                                                          2-(4-chlorophenyl)-2-cyclo-                                                                     100     100    100                                          pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       Comparison Agent                                                              2,3-dihydro-5-carbox-       97.5 <75                                          anilido-6-methyl-1,4-                                                         oxathiine-4,4-dioxide                                                         ______________________________________                                    

The compositions are provided at 10% or 20% formulations dispersible inwater.

Example 45

Effect of Prophylactic Leaf Treatment Against the Leaf-Spot DiseaseCerospora Beticola in Sugar Beets (Beta Vulgaris).

Sugar beet plants with four well developed leaf flakes are sprayed so asto become dripping wet with the given concentrations. After drying ofthe spray coatings, the treated plants as well as untreated controlplants are uniformly sprayed with a suspension of 15,000 cerocosporaspores per ml. At 26° C. and under water vapor-saturated air, the plantsare incubated four days in a greenhouse. Thereafter, at a temperature ofabout 22° C. they are kept an additional ten days in a greenhouse. Theportion of infected leaf surface is estimated.

    ______________________________________                                                          % Activity against Cercospora                               Compounds         beticola with Active Substance                              According         Concentration                                               to the Invention  500      100      ppm                                       ______________________________________                                        2-cyclohexyloxy-3-(imidazol-                                                                    100      --                                                 1-yl)-2-phenyl-propanenitrile                                                 2-cyclohexyloxy-3-(imidazol-                                                                     99      93                                                 1-yl)-2-phenyl-propanenitrile                                                 hydronitrate                                                                  2-(2-chlorophenyl)-2-cyclo-                                                                      93      --                                                 hexyloxy-3-(imidazol-1-yl)-                                                   propanenitrile                                                                2-(2-chlorophenyl)-2-cyclo-                                                                      97      86                                                 hexyloxy-3-(imidazol-1-yl)-                                                   propanenitrile, hydronitrate                                                  2-cyclohexyloxy-2-phenyl-3-                                                                     100      90                                                 (1,2,4-triazol-1-yl)-propane-                                                 nitrile                                                                       2-cyclohexyloxy-2-phenyl-3-                                                                     100      100                                                (1,2,4-triazol-1-yl)-propane-                                                 nitrile, hydronitrate                                                         2-(2-chlorophenyl)-2-cyclo-                                                                     100      83                                                 hexyloxy-3-(1,2,4-triazol-                                                    1-yl)-propanenitrile                                                          2-(2-chlorophenyl)-2-cyclo-                                                                     100      --                                                 hexyloxy-3-(1,2,4-triazol-                                                    1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       2-cyclopentyloxy-3-(imidazol-                                                                   100      99                                                 1-yl)-2-phenyl-propanenitrile                                                 2-cyclopentyloxy-3-(imidazol-                                                                   100      96                                                 1-yl)-2-phenyl-propanenitrile                                                 hydronitrate                                                                  2-(2-chlorophenyl)-2-cyclo-                                                                     100      99                                                 pentyloxy-3-(imidazol-1-                                                      yl)-propanenitrile, hydronitrate                                              2-cyclopentyloxy-2-phenyl-                                                                      100      100                                                3-(1,2,4-triazol-1-yl)-                                                       propanenitrile                                                                2-cyclopentyloxy-2-phenyl-                                                                      100      100                                                3-(1,2,4-triazol-1-yl)-                                                       propanenitrile, hydronitrate                                                  2-(2-chlorophenyl)-2-cyclo-                                                                     100      100                                                pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile                                                            2-(2-chlorophenyl)-2-cyclo-                                                                     100      100                                                pentyleoxy-3-(1,2,4-triazol-                                                  1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       2-cyclohexyloxy-2-(2,4-                                                                          99      93                                                 dichlorophenyl)-3-(imidazol-                                                  1-yl)-propanenitrile                                                          2-cyclohexyloxy-2-(2,4-                                                                          93      80                                                 dichlorophenyl)-3-(imidazol-                                                  1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       2-(4-chlorophenyl)-2-cyclo-                                                                     100      84                                                 hexyloxy-3-(1,2,4-triazol-                                                    1-yl)-propanentrile                                                           2-(4-chlorophenyl)-2-cyclo-                                                                     100      82                                                 hexyloxy-3-(1,2,4-triazol-                                                    1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       2-cyclohexyloxy-2-(2,4-                                                                         100      --                                                 dichlorophenyl)-3-(1,2,4-                                                     triazol-1-yl)-propanenitrile                                                  2-(4-chlorophenyl)-2-cyclo-                                                                     100      96                                                 pentyloxy-3-(imidazol-1-                                                      yl)-propanenitrile                                                            2-(4-chlorophenyl)-2-cyclo-                                                                     100      100                                                pentyloxy-3-(imidazol-1-yl)-                                                  peopanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclo-                                                                     100      100                                                pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile                                                          2-(4-chlorophenyl)-2-cyclo-                                                                     100      96                                                 pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       The compounds are provided as 10% or 20% formulations dis-                    persible in water.                                                            2-(2-chlorophenyl)-2-cyclopentyl-                                                               100      99                                                 oxy-3-(imidazol-1-yl)-propane-                                                nitrile                                                                       ______________________________________                                    

Example 46

Effect of Prophylactic Spray Treatment Against Fusarium Colmorum in ClubMillet (Setaria Italica).

Young millet plants of three to four cm height are sprayed dripping wetwith the given concentrations. After drying of the spray coatings, thetreated plants as well as untreated control plants are sprayed with a30% biomalt-containing aqueous suspension of fusarium spores (800,000per ml), and then incubated moist in a greenhouse at 20°-22° C. Aftersix days, the percent portion of infected leaf surface is estimated.

    ______________________________________                                                         % Activity against Fusarium                                  Compounds        culmorum with Active Substance                               According        Concentration                                                to the Invention 500         ppm                                              ______________________________________                                        2-cyclopentyloxy-3-(imidazol-                                                                  97                                                           1-yl)-2-(2-methylphenyl)-                                                     propanenitrile, hydronitrate                                                  2-cylcopentyloxy-2-(2-methyl-                                                                  97                                                           phenyl)-3-(1,2,4-triazon-1-                                                   yl)-propanenitrile, hydronitrate                                              2-cyclohexyloxy-3-(imidazol-1-                                                                 96                                                           yl)-2-(2-methylphenyl)-propane-                                               nitrile, hydronitrate                                                         2-cyclohexyloxy-2-(2-methyl-                                                                   91                                                           phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile, hydronitrate                                              2-cyclohexyloxy-3-(imidazol-1-                                                                 97                                                           yl)-2-(2-methylphenyl)-                                                       propanenitrile                                                                2-cyclohexyloxy-2-(2-methyl-                                                                   96                                                           phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile                                                            2-cyclopentylxoy-3-(imidazol-                                                                  99                                                           1-yl)-2-(2-methylphenyl)-                                                     propanenitrile                                                                2-cyclopentyloxy-2-(methyl-                                                                    97                                                           phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile                                                            2-cyclopentyloxy-3-(imidazol-                                                                  95                                                           1-yl)-2-phenyl-propanenitrile                                                 2-cyclopentyloxy-3-(imidazol-                                                                  90                                                           1-yl)-2-phenyl-propanenitrile,                                                hydronitrate                                                                  2-(2-chlorophenyl)-2-cyclo-                                                                    90                                                           pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile                                                                2-(2-chlorophenyl)-2-cyclo-                                                                    93                                                           pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclo-                                                                    97                                                           pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile                                                                2-(4-chlorophenyl)-2-cyclo-                                                                    95                                                           pentyl-oxy-3-(imidazol-1-yl)-                                                 propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclo-                                                                    90                                                           pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile                                                          2-(4-chlorophenyl)-2-cyclo-                                                                    95                                                           pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       ______________________________________                                    

The compounds are provided as 10% or 20% formulations dispersible inwater.

Example 47

Effect of Prophylactic Spray Treatment Against Botrytis Cinerea inTomato Plants.

Young tomato plants with at least two well developed leaf flakes aresprayed dripping wet with the given active substance concentrations.After drying of the spray coatings, the treated plants as well asuntreated control plants are innoculated by means of spraying of asuspension of about one million botrytis spores per ml fruit juicesolution. Subsequently the plants are incubated moist in a greenhouse atabout 20° C. After crumbling of the untreated plants (=100% infection)the degree of infection of the treated plants is determined.

    ______________________________________                                                           % Activity Against                                         Compounds          Botrytis cinerea with Active                               According to       Substance Concentration                                     the Invention     250        ppm                                             ______________________________________                                        2-(4-chlorophenyl)-2-cyclo-                                                                      80                                                         pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile                                                                2-(4-chlorophenyl)-2-cyclo-                                                                      80                                                         pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile, hydronitrate                                                  Comparison Agent from                                                         DE-OS 26 04 047                                                               2-(imidazol-1-yl-methyl)-2-phenyl-                                                                5                                                         hexanenitrile hydronitrate                                                    ______________________________________                                    

Example 48

Effect of Prophylactic Spray Treatment Against Helminthosporium Teres(pyrenophora teres) in Barley.

Young barley plants in the stage of the first leaves are sprayeddripping wet with the given concentrations. After drying of the spraycoatings, the treated plants as well as untreated control plants aresprayed with an aqueous conidiospore suspension (about 50,000 per ml) ofHelminthosporium Teres and then incubated in a moisture-chamber in agreenhouse for a period of two days at 20°-22° C. Thereafter the plantsare cultivated in a greenhouse at about 20°-22° C. One week after theinnoculation, the percent portion of infected leaf surface is estimated.

    ______________________________________                                                      % Activity Against Helminthosporium                             Compounds     Teres with Active Substance                                     According to  Concentration                                                   the Invention 500           ppm                                               ______________________________________                                        2-cyclopentyloxy-3-                                                                         80                                                              (imidazol-1-yl)-2-(2-                                                         methylphenyl-propane-                                                         nitrile, hydronitrate                                                         2-cyclohexyloxy-3-                                                                          80                                                              (imidazol-1-yl)-2-                                                            (2-methylphenyl)-                                                             propanenitrile                                                                2-cyclohexyloxy-2-                                                                          80                                                              (2-methylphenyl)-3-                                                           (1,2,4-triazol-1-yl)-                                                         propanenitrile                                                                ______________________________________                                    

Example 49

Effect of Prophylactic Spray Treatment Against Cochlliobolus Miyabeanusin Rice Plants.

Young rice plants in the stage of the start of the second leaves aresprayed dripping wet with the given concentrations. After drying of thespray coatings, the treated plants as well as untreated control plantsare sprayed with an aqueous conidia suspension (about 250,000 per ml) ofthe fungus, and then incubated moist in a greenhouse at about 24° C.After four days the percent portion of the infected leaf surface isnoted.

    ______________________________________                                                         % Activity Against Cochliobolus                              Compounds        miyabeanus with Active                                       According to     Substance Concentration                                      the Invention    500         ppm                                              ______________________________________                                        2-cyclopentyloxy-3-(imidazol-                                                                  80                                                           1-yl)-2-(2-methylphenyl)-                                                     propanenitrile, hydronitrate                                                  2-cyclopentyloxy-2-(2-                                                                         80                                                           methylphenyl)-3-(1,2,4-triazol-                                               1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       2-cyclohexyloxy-3-(imidazol)-                                                                  80                                                           1-yl)-2-(2-methylphenyl)-                                                     propanenitrile, hydronitrate                                                  2-cyclohexyloxy-2-(2-methyl-                                                                   80                                                           pehnyl)-3-(1,2,4-triazol-                                                     1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       2-cyclohexyloxy-3-(imidazol-                                                                   80                                                           1-yl)-2-(2-methylphenyl)-                                                     propanenitrile                                                                2-cyclohexyloxy-2-(2-methyl-                                                                   80                                                           phenyl)-3-(1,2,4-triazol-                                                     1-yl)-propanenitrile                                                          2-cyclopentyloxy-3-(imidazol-                                                                  80                                                           1-yl)-2-(2-methylphenyl)-                                                     propanenitrile                                                                ______________________________________                                    

Example 50

Effect of Prophylactic Spray Treatment Against Phytophthora Infestans inTomato Plants.

Young tomato plants with at least two well developed leaf flakes aresprayed dripping wet. After drying of the spray coatings, the treatedplants as well as unctreated control plants are sprayed with an aqueoussuspension of about 80,000 phytophthora sporangia per ml, the suspensionhaving been incubated for two hours at 11° C. The plants are thenincubated moist in a greenhouse at about 18° C. After five days thepercent portion of infected leaf surface is estimated.

    ______________________________________                                                        % Activity Against Phytophthora                               Compound        infestans with Active Substance                               According to    Concentration                                                 the Invention   500          ppm                                              ______________________________________                                        2-cyclohexyloxy-2-phenyl-                                                                      91                                                           3-(1,2,4-triazol-1-yl)-                                                       propanenitrile                                                                ______________________________________                                    

Example 51

Activity Against Apple Scab (Venturia inequalis), Prophylactic andCurative.

The five youngest leaves of apple shoots planted in free acreage aretreated dripping wet. After drying of the spray coatings, these shootsas well as untreated shoots are sprayed with a suspension of 320,000conidiospore of the fungus per ml 3% glucose solution in distilledwater, and then confined for a period of 53 hours in polyethylene sacksunder shade. Eight days after the innoculation a number of theuntreated, innoculated shoots are subjected to a curative treatment(dripping wet). Five weeks after the innoculation the percent degree ofscab covering on the leaf surfaces is estimated.

    ______________________________________                                                           % Activity Against Apple                                                      Scab with Active Substance                                 Compound           Concentration                                              According to       750     ppm                                                the Invention      Prophylactic                                                                              Curative                                       ______________________________________                                        2-cyclopentyloxy-3-                                                                              100         86                                             (imidazol-1-yl)-2-(2-                                                         methylphenyl)-propane-                                                        nitrile                                                                       Control (untreated)                                                                              35% infection                                              ______________________________________                                                           % Activity Against Apple Scab                                                 with Active Substance                                      Compounds          Concentration                                              According to                   300 ppm                                        the Invention      Prophylactic                                                                              Curative                                       ______________________________________                                        2-cyclopentyloxy-3-(imidazol-                                                                    86          --                                             1-yl)-2-(2-methylphenyl)-                                                     propanenitrile                                                                2-cyclohexyloxy-3-(imidazol-                                                                     98          --                                             1-yl)-2-phenyl-propanenitrile                                                 2-cyclohexyloxy-3-(imidazol-                                                                     90          --                                             1-yl)-2-phenyl-propanenitrile,                                                hydronitrate                                                                  2-cyclopentyloxy-3-(imidazol-                                                                    97          81                                             1-yl)-2-phenyl-propanenitrile                                                 2-cyclopentyloxy-3-(imidazol-                                                                    91          90                                             1-yl)-2-phenyl-propanenitrile,                                                hydronitrate                                                                  2-cyclopentyloxy-2-phenyl-3-                                                                     100         95                                             (1,2,4-triazol-1-yl)-propane-                                                 nitrile                                                                       2-cyclopentyleoxy-2-phenyl-3-                                                                    100         90                                             (1,2,4-triazol-1-yl)-propane-                                                 nitrile, hydronitrate                                                         2-(2-chlorophenyl)-2-cyclo-                                                                      98          73                                             pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile                                                            2-(2-chlorophenyl)-2-cyclo-                                                                      88          --                                             pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile, hydronitrate                                            2-cychlohexy-2-(2,4-dichloro-                                                                    84          --                                             phenyl)-3-(imidazol-1-yl)-pro-                                                panenitrile                                                                   2-(4-chlorophenyl)-2-cyclo-                                                                      100         93                                             hexyloxy-3-(1,2,4-triazol-1-                                                  yl)-propaneitrile                                                             2-(4-chlorophenyl)-2-cyclo-                                                                      100           99.5                                         hexyloxy-3-(1,2,4-triazol-                                                    1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       2-(4-chlorophenyl)-2-cyclo-                                                                      96          99                                             pentyloxy-3-(imidazol-1-                                                      yl)-propanenitrile                                                            2-(4-chlorophenyl)-2-cyclo-                                                                      89          95                                             pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclo-                                                                        99.5      94                                             pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile                                                          2-(4-chlorophenyl)-2-cyclo-                                                                      100         99                                             pentylxoy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile, hydro-                                                    nitrate                                                                       ______________________________________                                    

The following operational examples serve for illustration of usepossibilities of the compounds according to the present invention asgrowth regulators:

Example 52

Growth-regulatory Effect with Sugar Beets.

Sugar beets are treated in a pre-germination technique with a calculated0.5 kg active substances per ha, and then further cultivated in agreenhouse. Eight days after the application, the percent restraint ofgrowth is determined as the influence of the preparation.

    ______________________________________                                        Compounds                                                                     According          Percent Growth                                             to the Invention   Restraint                                                  ______________________________________                                        2-cyclohexyloxy-2-(2-                                                                            40                                                         methylphenyl)-3-(1,2,4-triazol-                                               1-yl)-propanenitrile, hydro-                                                  nitrate                                                                       2-cyclohexyloxy-2-(2-methyl-                                                                     20                                                         phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile                                                            Control             0                                                         ______________________________________                                    

The treatment of the plants leads to a growth restraint and a dark greencoloration of the leaves.

Example 53

Growth Regulation with Sugar Beets and Corn.

Corn and sugar beets are placed in a greenhouse after a pre-germinationspraying with the substances according to the present invention. Elevendays after the treatment, growth-regulatory effects are determined byway of the percent growth restraint. 0.5 kg active substance per ha ledto the following results:

    ______________________________________                                        Compounds           Percent Growth                                            According to        Restraint                                                 the Invention       Corn   Sugar Beets                                        ______________________________________                                        2-(2-chlorophenyl)-2-cyclo-                                                                       14     14                                                 hexyloxy-3-(imidazol-1-yl)-                                                   propanenitrile                                                                2-(2-chlorophenyl)-2-cyclo-                                                                       21     14                                                 hexyloxy-3-(imidazol-1-yl)-                                                   propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclo-                                                                       14     14                                                 hexyloxy-3-(imidazol-1-yl)-                                                   propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclo-                                                                       21     29                                                 pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile                                                                2-(4-chlorophenyl)-2-cyclo-                                                                       36     57                                                 pentyloxy-3-(1,2,4-triazol-                                                   1-yl)-propanenitrile                                                          Control              0      0                                                 ______________________________________                                    

The results show that the substances according to the present inventionclearly restrain the longitudinal growth of the treated plants.

Example 54

Effect of Prophylactic Leaf Treatment Against Plasmopara viticola withGrape Plants in a Greenhouse.

Young grape plants with about 5 to 8 leaves are sprayed dripping wetwith 500 ppm active substance concentration. After drying of the spraycoatings, the undersides of the leaves are sprayed with an aqueousdeposit of sporangia of the fungus (about 55,000 per ml), and thenincubated in a greenhouse at 22°-24° C. in an atmosphere as watervapor-saturated as possible.

From the second day, the air moisture is brought back to a normal level(30 to 70% saturation) for a period of 3-4 days, and then held at watervapor-saturation for 1 further day. Subsequently each leaf is evaluatedinsofar as the percent portion of fungus-infected surface, and theaverage per treatment is used for determination of the fungicidalactivity as described above.

    ______________________________________                                        Compounds                                                                     According to        Activity Against                                          the Invention       Plasmopara viticola                                       ______________________________________                                        2-cyclopentyloxy-3-(imidazol-                                                                     89                                                        1-yl)-2-(2-methylphenyl)-                                                     propaneitrile, hydronitreat                                                   2-cyclopentyloxy-2-(2-methyl-                                                                     84                                                        phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile, hydronitrate                                              2-cyclohexyloxy-3-(imidazol-1-                                                                    100                                                       yl)-2-(2-methylphenyl)-                                                       propanenitrile, hydronitrate                                                  2-cyclohexyloxy-2-(2-methyl-                                                                      85                                                        phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile, hydronitrate                                              2-cyclohexyloxy-2-phenyl-3-                                                                       91                                                        (1,2,4-triazol-1-yl)-propanenitrile                                           2-cyclohexyloxy-3-  95                                                        (imidazol-1-yl)-2-(2-methyl-                                                  phenyl)-propanenitrile                                                        2-cyclohexyloxy-2-(2-methyl-                                                                      91                                                        phenyl)-3-(1,2,4-triazol-1-                                                   yl)-propanenitrile                                                            2-cyclopentyloxy-3-(imidazol-                                                                     98                                                        1-yl)-2-(2-methylphenyl)-                                                     peopanenitrile                                                                2-cyclopentyloxy-3-(imidazol-                                                                     100                                                       1-yl)-2-phenyl-propanenitrile                                                 2-cyclopentyloxy-3-(imidazol-                                                                     73                                                        1-yl)-2-phenyl-propanenitrile,                                                hydronitrate                                                                  2-(2-chlorophenyl)-2-cyclo-                                                                       90                                                        pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile                                                                2-(2-chlorophenyl)-2-cyclo-                                                                       97                                                        pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile, hydronitrate                                                  2-cyclopentyloxy-2-phenyl-3-                                                                      95                                                        (1,2,4-triazol-lyl)-propane-                                                  nitrile                                                                       2-cyclopentyloxy-2-phenyl-3-                                                                      98                                                        (1,2,4-triazol-1-yl)-propane-                                                 nitrile, hydronitrate                                                         2-(2-chlorophenyl)-2-cyclo-                                                                       98                                                        pentyloxy-3-(1,2,4-triazol-1-yl)-                                             propanenitrile                                                                2-(4-chlorophenyl)-2-cyclo-                                                                       99.5                                                      pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile                                                                2-(4-chlorophenyl)-2-cyclo-                                                                       100                                                       pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclo-                                                                       97                                                        pentyloxy-3-(1,2,4-triazol-1-yl)-                                             poropanenitrile                                                               2-(4-chlorophenyl)-2-cyclo-                                                                       85                                                        pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile, hydro-                                                    nitrate                                                                       ______________________________________                                    

The agents according to the invention are provided as 10% or 20%formulations dispersible in water.

Example 55

Activity in vitro Against Mucor spec. of Soybeans.

Aqueous preparations of the active substances are mixed with sterilized,liquid agar nutrient base (2% biomalt, 2% agar) at about 45° C. in suchmanner that the mixture contains 250 ppm active substance. The mixtureis then placed in polystyrene petri dishes of 8.5 cm diam. to a heightof 5 mm. After cooling of the nutrient base, each petri dish is providedwith a 5 mm diam. agar piece overgrown with Mucor. Per treatment, twodishes and also four untreated dishes are inoculated.

After five days incubation at 22° C. in the dark, the colony diametersare measured and after removal of the inoculate quantity of 5 mm,employed as follows for calculation of the fungicidal activity: ##EQU2##

    ______________________________________                                        Compounds                                                                     According to        % Activity Against                                        the Invention       Mucor Spec.                                               ______________________________________                                        2-cyclopentyloxy-2-(2-methyl-                                                                     80                                                        phenyl)-3-(1,2,4-triazol-1-yl)-                                               propanenitrile, hydronitrate                                                  2-cyclopentyloxy-3-(imidazol-                                                                     75                                                        1-yl)-2-(2-methylphenyl)-                                                     propanenitrile                                                                2-cyclohexyloxy-2-phenyl-                                                                         100                                                       3-(1,2,4-triazol-1-yl)-                                                       propanenitrile                                                                2-cyclopentyloxy-3-(imidazol-                                                                     95                                                        1-yl)-2-phenyl-propanenitrile                                                 2-(2-chlorophenyl)-2-cyclo-                                                                       94                                                        pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile                                                                2-cyclopentyloxy-2-phenyl-                                                                        100                                                       3-(1,2,4-triazol-1-yl)-                                                       propanenitrile                                                                2-cyclopentyloxy-2-phenyl-                                                                        75                                                        3-(1,2,4-triazol-1-yl)-                                                       propanenitriel, hydronitrate                                                  2-(2-chlorophenyl)-2-cyclo-                                                                       98                                                        pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile                                                            2-(4-chlorophenyl)-2-cyclo-                                                                       100                                                       pentyloxy-3-(imidazol-1-                                                      yl)-propanenitrile                                                            2-(4-chlorophenyl)-2-cyclo-                                                                       77                                                        pentyloxy-3-(imidazol)1-                                                      yl)-propanenitrile, hydronitrate                                              2-(4-chlorophenyl)-2-cyclo-                                                                       100                                                       pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile                                                            2-(4-chlorophenyl)-2-cyclo-                                                                       87                                                        pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile, hydronitrate                                              Comparison agent                                                              2-cyano-2-methoxyiminoacetic                                                                      50                                                        acid ethylaminocarbonylamide                                                  ______________________________________                                    

The agents according to the invention are provided as 10% or 20%formulations dispersible in water.

Example 56

Effect in vitro Against Pseudomonas phaseolicola (Fat Spot Disease ofBeans).

Aqueous preparations of the active substances are mixed with sterilized,liquid agar base (2% biomalt, 2% agar) at about 56° C. in such mannerthat the mixtures contain 50 ppm active substance. The mixtures are thenplaced in polystyrene petri dishes of 8.5 cm. diam. to a height of 5 mm.After cooling of the nutrient base, the middle of each petri dish isdabbed with a suspension of pseudomonas phaseolicola in distilled waterby means of 5 mm. quantity inoculation loop. Per treatment, two dishesand four untreated dishes are inoculated. After four and one half weeksincubation at 20°-22° C. in the dark, the colony diameters aredetermined. After withdrawal of the inoculate quantity, the colonies areemployed as follows for a calculation of bactericidal activity: ##EQU3##

    ______________________________________                                        Compounds                                                                     According to       % Activity Against                                         the Invention      Pseudomonas phaseolicola                                   ______________________________________                                        2-(2-chlorophenyl)-2-cyclo-                                                                      82                                                         pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile, hydronitrate                                                  2-cyclopentyloxy-2-phenyl-3-                                                                     73                                                         (1,2,4-triazol-1-yl)-propane-                                                 nitrile                                                                       2-cyclopentyloxy-2-phenyl-                                                                       91                                                         3-(1,2,4-triazol-1-yl)-                                                       propanenitrile, hydronitrate                                                  2-(2-chlorophenyl)-2-cylco-                                                                      91                                                         pentyloxy-3-(1,2,4-triazol-1-yl)-                                             propanenitrile                                                                2-(4-chlorophenyl)-2-cyclo-                                                                      100                                                        pentyloxy-3-(imidazol-1-                                                      yl)-propanenitrile                                                            2-(4-chlorophenyl)-2-cyclo-                                                                      100                                                        pentyloxy-3-(imidazol-1-yl)-                                                  propanenitrile, hydronitrate                                                  2-(4-chlorophenyl)-2-cyclo-                                                                      91                                                         pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile                                                            2-(4-chlorophenyl)-2-cyclo-                                                                      91                                                         pentyloxy-3-(1,2,4-triazol-1-                                                 yl)-propanenitrile, hydronitrate                                              Comparison Agent                                                              2-cyano-2-methoxyiminoacetic                                                                      0                                                         acid-ethylaminocarbonylamide                                                  ______________________________________                                    

The agents according to the invention are provided as 10% or 20%formulations dispersible in water.

It will be understood that each of the elements described above, or twoor more together, will also find a useful application in other types ofbiocidal preparation differing from the types described above.

While the invention has been illustrated and described as embodied inazolyl-propanenitriles, processes for the production of these compoundsas well as biocidal compositions containing the same, it is not intendedto be limited to the details shown, since various modifications andstructural changes may be made without departing in any way from thespirit of the present invention.

Without further analysis, the foregoing will so fully reveal the gist ofthe present invention that others can, by applying current knowledge,can readily adapt it for various applications without omitting featuresthat, from the standpoint of prior art, fairly constitute essentialcharacteristics of the generic and specific aspects of this invention.

What is desired to be protected by Letters Patent is set forth in theappended claims.

We claim:
 1. Azolyl-propanenitrile of the formula ##STR7## in which R isphenyl, methylphenyl, fluorophenyl, chlorophenyl or dichlorophenyl,R₁ iscyclopentyl or cyclohexyl, and Y is N or CH, or a salt thereof withnitric acid.
 2. The compound according to claim 1 wherein R is2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl,3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl,2,6-dichlorophenyl, 2-methylphenyl, 3-methylphenyl, or 4-methylphenyl,R₁is cyclopentyl or cyclohexyl, and Y is N or CH.
 3. The compoundaccording to claim 1,2-cyclopentyloxy-3-(imidazol-1-yl)-2-(2-methylphenyl)-propanenitrile,hydronitrate.
 4. The compound according to claim 1,2-cyclopentyloxy-3-(imidazol-1-yl)-2-phenyl-propanenitrile,hydronitrate.
 5. The compound according to claim 1,2-cyclopentyloxy-2-phenyl-3-(1,2,4-triazol-1-yl)-propanenitrile,hydronitrate.
 6. The compound according to claim 1,2-(2-chlorophenyl)-2-cyclopentyloxy-3-(1,2,4-triazol-1-yl)-propanenitrile,hydronitrate.
 7. The compound according to claim 1,2-(4-chlorophenyl)-2-cyclopentyloxy-3-(imidazol-1-yl)-propanenitrile,hydronitrate.
 8. The compound according to claim 1,2-(4-chlorophenyl)-2-cyclopentyloxy-3-(1,2,4-triazol-1-yl)-propanenitrile,hydronitrate.
 9. A fungicidal, plant growth regulating and bactericidalcomposition comprising from 10 to 90 percent by weight of at least onecompound according to claim 1 in mixture with a carrier material, withor without an adjuvant.
 10. Method or protecting plants against fungi,comprising applying onto or within the locus of said plants afungicidally-effective amount of the composition according to claim 9.11. Method of regulating the growth of plants, comprising applying ontoor within the locus of said plants a growth-regulatory-effective amountof the composition according to claim
 9. 12. Method of protecting plantsagainst bacteria, comprising applying onto or within the locus of saidplants a bactericidally-effective amount of the composition according toclaim 9.